JP2021527055A - HCFC−244bbを脱塩化水素化してHFO−1234yfを製造する方法 - Google Patents
HCFC−244bbを脱塩化水素化してHFO−1234yfを製造する方法 Download PDFInfo
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 95
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 238000007033 dehydrochlorination reaction Methods 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 59
- 238000004821 distillation Methods 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 230000008016 vaporization Effects 0.000 claims description 16
- 238000000926 separation method Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 238000004064 recycling Methods 0.000 claims description 7
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 5
- 230000008021 deposition Effects 0.000 claims description 5
- 238000010586 diagram Methods 0.000 abstract description 5
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000009834 vaporization Methods 0.000 description 12
- 238000007654 immersion Methods 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 239000012671 ceramic insulating material Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 2
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 2
- 229910000881 Cu alloy Inorganic materials 0.000 description 2
- 229910000640 Fe alloy Inorganic materials 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000000788 chromium alloy Substances 0.000 description 2
- BIJOYKCOMBZXAE-UHFFFAOYSA-N chromium iron nickel Chemical compound [Cr].[Fe].[Ni] BIJOYKCOMBZXAE-UHFFFAOYSA-N 0.000 description 2
- OGSYQYXYGXIQFH-UHFFFAOYSA-N chromium molybdenum nickel Chemical compound [Cr].[Ni].[Mo] OGSYQYXYGXIQFH-UHFFFAOYSA-N 0.000 description 2
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000004088 foaming agent Substances 0.000 description 2
- -1 heat transfer media Substances 0.000 description 2
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 description 1
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【選択図】図1
Description
96.0重量%の244bb、3.5重量%の1233xf、及び0.5重量%の他の材料(ガスクロマトグラフにより測定される)を含む組成物を、70psigで少なくともその露点まで気化させた。気化した組成物を熱交換器で過熱し、次いで、過熱器で900°Fまで更に過熱した。更に過熱された気化した組成物を、4つの電気的に加熱されたセクションを含む反応器に導入した。過熱器は、過熱器内のコーキングを最小化するために、ガス速度が、反応器内のガス速度の少なくとも2倍になるように構成した。反応器内の加熱器表面温度は、平均加熱器表面温度995°Fで993°F〜997°Fに維持した。過熱された気化した組成物は、反応器への入口条件に基づいて、平均接触時間5.46秒で反応器を通過した。反応器の出力を蒸留カラムに導いて、未反応の244bbを1234yf及びHClから分離した。未反応の244bbを含む蒸留出力の底部流をリサイクルのために回収した。1234yf及びHClを含むオーバーヘッド流を別の蒸留カラムに導いて、HClをオーバーヘッド生成物として分離し、1234yfを含む粗生成物流を生成した。プロセスは、21.3%の204bbから1234yfへの全体的な変換のために80時間維持した。当該技術分野において周知の技術を使用して、生成物流をガスクロマトグラフにより分析した。結果を以下の表に示す。
実施例2
実施例3
比較実施例
Claims (3)
- 2,3,3,3−テトラフルオロプロペン(HFO−1234yf)を作製するためのプロセスであって、前記プロセスは、
約850°F(454℃)を超える表面温度の加熱器表面を含む反応器に、2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を含む組成物を供給することと、
10秒未満の接触時間で前記組成物を前記加熱器表面に接触させて、前記HCFC−244bbの一部を脱塩化水素化してHFO−1234yfを作製することと、を含む、プロセス。 - 前記HCFC−244bbの前記一部の前記脱塩化水素化が塩酸(HCl)を生成し、前記プロセスが、
前記HFO−1234yf、HCl、及び未反応のHCFC−244bbを前記反応器から蒸留カラムに供給することと、
前記蒸留カラム内で前記HFO−1234yf及び前記HClを前記HCFC−244bbの少なくとも一部から分離することと、
前記分離したHCFC−244bbを前記反応器にリサイクルすることと、
前記HFO−1234yf及び前記HClをHCl分離ユニットに供給することと、
前記HClを前記HFO−1234yfから分離して、前記HFO−1234yfを含む生成物流を形成することと、を更に含み、
前記生成物流が、HCFC−244bbを含まずに99.1重量%超の濃度の前記HFO−1234yfと、前記反応器内での低率のカーボン堆積を示すものとして、HCFC−244bbを含まずに0.1重量%未満の濃度の1,1,1,2−テトラフルオロエタンと、を含む、請求項1に記載のプロセス。 - 2,3,3,3−テトラフルオロプロペン(HFO−1234yf)を作製するためのプロセスであって、前記プロセスは、
2−クロロ−1,1,1,2−テトラフルオロプロパン(HCFC−244bb)を含む組成物を気化させることと、
前記組成物を第1の部分及び第2の部分に分割することと、
前記気化した組成物の前記第1の部分を約575°F(302℃)〜1,200°F(649℃)の温度に加熱することと、
約850°F(454℃)を超える表面温度の加熱器表面を含む反応器に前記組成物を供給することであって、前記反応器が、第1の段と、前記第1の段の下流の第2の段とを含み、前記第1の部分は前記第1の段に供給され、前記第2の部分は前記第2の段に供給される、ことと、
10秒未満の接触時間で前記組成物を前記加熱器表面に接触させて、前記HCFC−244bbの一部を脱塩化水素化してHFO−1234yfを作製することと、を含む、プロセス。
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US201816001728A | 2018-06-06 | 2018-06-06 | |
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PCT/US2019/035609 WO2019236720A1 (en) | 2018-06-06 | 2019-06-05 | Method for dehydrochlorination of hcfc-244bb to manufacture hfo-1234yf |
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JP2024035459A Pending JP2024069358A (ja) | 2018-06-06 | 2024-03-08 | HCFC-244bbを脱塩化水素化してHFO-1234yfを製造する方法 |
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US (2) | US11555001B2 (ja) |
EP (2) | EP4212500A1 (ja) |
JP (2) | JP2021527055A (ja) |
KR (1) | KR20210008102A (ja) |
CN (1) | CN112313199A (ja) |
WO (1) | WO2019236720A1 (ja) |
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- 2019-06-05 JP JP2020567862A patent/JP2021527055A/ja active Pending
- 2019-06-05 WO PCT/US2019/035609 patent/WO2019236720A1/en unknown
- 2019-06-05 US US16/972,473 patent/US11555001B2/en active Active
- 2019-06-05 CN CN201980040695.7A patent/CN112313199A/zh active Pending
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WO2019236720A1 (en) | 2019-12-12 |
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CN112313199A (zh) | 2021-02-02 |
EP3814312A4 (en) | 2022-03-02 |
EP3814312A1 (en) | 2021-05-05 |
US11555001B2 (en) | 2023-01-17 |
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